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Phenylacetaldehyde is an organic compound used in the synthesis of fragrances and polymers. [1] Phenylacetaldehyde is an aldehyde that consists of acetaldehyde bearing a phenyl substituent; the parent member of the phenylacetaldehyde class of compounds.
Phenylglyoxal was first prepared by thermal decomposition of the sulfite derivative of the oxime: [5]. C 6 H 5 C(O)CH(NOSO 2 H) + 2 H 2 O → C 6 H 5 C(O)CHO + NH 4 HSO 4. More conveniently, it can be prepared from methyl benzoate by reaction with KCH 2 S(O)CH 3 to give PhC(O)CH(SCH 3)(OH), which is oxidized with copper(II) acetate. [6]
[3] [4] In both species, it is subsequently metabolized into 4-hydroxyphenylacetate by aldehyde dehydrogenase (ALDH) enzymes in humans and the phenylacetaldehyde dehydrogenase (feaB) enzyme in E. coli. [3] [4] [5] The condensation of 4-hydroxyphenylacetaldehyde and dopamine is a key step in the biosynthesis of benzylisoquinoline alkaloids.
The hydroformylation of methanol with catalysts like cobalt, nickel, or iron salts also produces acetaldehyde, although this process is of no industrial importance. Similarly noncompetitive, acetaldehyde arises from synthesis gas with modest selectivity. [24]
These compounds are important in the synthesis of heterocyclic compounds. The analogous 1,4-addition of an aldehyde to an enone is called the Stetter reaction . In biochemistry , the coenzyme thiamine is responsible for biosynthesis of acyloin-like compounds utilizing the benzoin addition.
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